While guest-hosting a TV variety show in 1964, Dean Martin ridiculed a hot new rock ’n’ roll act with his trademark blend of cocksure innuendo, aw-shucks buffoonery, and inebriated syntax: “Now, something for the youngsters — five singing boys from England. . . . They’re called the Rollin’ Stones. I been rolled while I was stoned myself, so [pause, audience laughter] I don’t know what they’re singing about, but here they are at.” After the lads performed Willie Dixon’s “I Just Want to Make Love to You,” Dino ushered them offstage, quipping, “They’re gonna leave right after the show for London — they’re challenging the Beatles to a hair-pullin’ contest.” Years later, bassist Bill Wyman, still miffed, recalled another zinger from that day, when Martin described a trampoline acrobat as “the father of the Rolling Stones. He’s been trying to kill himself ever since.”

Imagine: A band that made its bones by being offensive taking offense at a disrespectful elder. Perhaps they consoled themselves by imagining that the crooner was whistling past the graveyard of musical obsolescence; actually, they were just too young to appreciate a kindred spirit, a performer whom no less an expert than Elvis Presley had dubbed “The King of Cool.” With the release of The Dean Martin Celebrity Roasts Collectors Edition (StarVista, six DVDs, $59.95), you can judge anew whether the tall, dark, and handsome baritone born Dino Paul Crocetti in Steubenville, Ohio, still deserved his crown as he and his cronies yukked it up during the twilight of an improbable, uniquely American, career.

In his magisterial biography Dino, author Nick Tosches describes Martin (1917–1995) as a natural-born singer who expanded effortlessly into nightclub comedy and a wide variety of roles on the silver screen. But despite his fabulous wealth and perennial popularity, Martin, according to Tosches, found little solace and even less meaning in his boundless success, maturing into what Dino’s hoodlum pals termed a menefreghista, Italian for someone “who simply did not give a fuck.” In his early singing career Martin was serendipitously teamed with a rubber-faced comic named Jerry Lewis, and their ad-libbed mayhem was an instant smash on the high-rolling nightclub circuit. In 1948, Dean began landing his songs on the pop charts; during the next year, he and Lewis embarked on a lucrative string of ludicrous comedies on the big screen. Lewis once said, with little financial exaggeration, “Can you pay two men $9 million to say ‘Did you take a bath this morning?’ ‘Why, is there one missing?’ — Do you dare contemplate such a fuck and duck? Yet that’s what we did.”

The act broke up acrimoniously in 1956, but by then Dean already had a bundle of top-10 songs, and there were plenty of solo roles awaiting him in Hollywood. Although Martin’s performances received decidedly mixed reviews, he was vindicated by boffo box office. The star was laconic about his acting style; later in his career, one director told Look magazine, “Dean doesn’t like acting, really. We set scenes up so that he only has to work in short spurts.” In the same article Dean dismissed method acting: “Motivation is a lotta crap.”

In 1965, when NBC introduced The Dean Martin Show, Dean found his true metier: indifference. The crooner opened with his mega-hit “Everybody Loves Somebody,” which the year before had knocked “A Hard Day’s Night” out of Billboard’s No. 1 slot and remained there for eight weeks. For his premiere, however, Dean warbled only a few bars, quipping, “No point in singing the whole song; you might not buy the record.” Next up: Dean and his guests cracking wise around a set built to look like a bar, a duet with old pal Frank Sinatra, and plenty of jiggling cleavage and high-stepping gams.

In its review, the Christian Science Monitor sniffed that if Dean “were anymore relaxed, he’d fall on his face,” adding, “One wondered, watching Dean, whether this man cared whether his show went over or not.” But, as Tosches relates in his filigreed prose, “the Dean Martin Show was an immense and immediate success. His uncaring manner and good-natured boorishness endeared him to the millions who were sick of sincerity, relevance, and pseudosophistication. Dean was a man whose success and fortune no man begrudged him. He seemed somehow kindred, one of them but blessed beyond them by the Fates. In him, for one late hour before the final day of every workweek, the multitudes, tired and half-drunk and onward-slouching, found something of their own: lullaby and vindication, justification and inspiration, a bit of boozy song and a glimpse of gal-meat.”

In 1973, producers brought the format of the New York Friars Club roast to the show, relieving Dean of any preparation at all save donning a tux and keeping his glasses handy for reading cue cards. Between that year and 1984, Dean hosted more than 50 roasts, 12 of which appear on The Dean Martin Celebrity Roasts Collectors Edition DVDs, and they offer a time capsule of comedy spanning from vaudeville throwbacks Jack Benny and George Burns right up through some of the era’s hottest comics, including Flip Wilson, Rowan and Martin, and Freddie Prinze. The formula is simple: An announcer welcomes a bevy of roasters — some of whom, such as standup comics Don Rickles, Phyllis Diller, and Nipsey Russell, and impressionist Rich Little, were basically regulars — followed by host Dino and the Man or Woman of the Week. The gang chortles amid a haze of cigarette smoke and everyone hoists drinks like it’s the fall of Rome, but what really redlines the Wayback Machine are the jokes. For the Sammy Davis Jr. roast, Dino’s opening quip imagines the NBC peacock wearing an afro, the first salvo in a barrage of cracks about the Klan, riding in the back of the bus, and Davis’s copious jewelry. There are also digs about Sammy’s obsequiousness toward Sinatra, a spectral presence in these 12 roasts, notable for his atrophied sense of humor. Comedian Jan Murray emphasized Ol’ Blue Eyes’s vindictiveness by warning Davis that if he kept closing his Vegas act with “My Way,” Sinatra’s signature tune, “You’ll wake up tomorrow morning with the head of a watermelon on your bed.”

Everyone on the dais was hip enough to acknowledge the malevolence of racism while also accepting it as an ongoing way of life in these United States, a sort of “use those ignorant rednecks for material” attitude. Occasionally, African-American performers inverted the formula, as when Sanford and Son’s Demond Wilson pretended to forget roastee Jack Benny’s name, saying, “You’re that nice Jewish boy who used to be on Rochester’s show.” Wilson added, with an exaggerated stage smile, that Benny had done much for black people in America: “Before Jack came along, everybody thought blacks were only fit to be shoeshine boys and railway porters. The Jack Benny program proved to America that they could also be chauffeurs, dishwashers, and houseboys.” Finally, pointing out that the black characters on the old Amos ’n’ Andy radio show were played by whites, Wilson called Benny a visionary, who’d hired a black actor to play Rochester on his radio show because “he knew that television was coming and it would’ve cost him a fortune in burnt cork.”

One repeated Rickles shtick is shouting gibberish in the cadences of an African-American preacher; he would then face the camera with an “I don’t understand what they’re saying either” shoulder shrug. But when Rickles heckled Muhammad Ali during a 1976 roast, the heavyweight champ rounded his gaze upon the comedian, who immediately turned subservient: “I drive the school bus and you go to school.”

Ali replied, “You’re not as dumb as you look, boy.”

Some jokes reveal the inroads of gay lib on the nation’s consciousness, as in Orson Welles’s louche surprise as he performs a dramatic reading of Dean’s hit song “That’s Amore”: “‘Like a GAY tarantella’? Apparently Dean has a side we know nothing about.” But the proceedings become more antediluvian when Rickles, in the same roast, professes, “I love my wife. [Pause] But my wife is ill,” and then introduces blonde Police Woman star Angie Dickinson with “I’d like to bring on this girl. And when we bring her on, let’s have the whole dais attack her.”

You know we are in the age before MADD when Gabe Kaplan, of Welcome Back, Kotter fame, jokes that he was going to enter Dean in the Drunken Olympics Decathlon: “Ten drunks trying to find their cars.” And woe to the comic who had to follow any of Foster Brooks’s inebriated alter egos, including Jack Benny’s accountant, Martin’s Boy Scout master, Jackie Gleason’s personal physician, or, most uproariously, the illicit lover of Rickles’s wife: “Don, I really must compliment you on your spouse, Missus [burp] Missus Pickles. I say that because she’s a real dilly. And I must also admit you have a very lovely home. Incidentally, you’re out of scotch.” It is great fun to watch Brooks stumble into character as he approaches the podium, and then, when his crapulous bit ends, straighten up and stride back to his seat, suave in his neatly trimmed beard and silvery mane, looking like the prototype for the Dos Equis “Most Interesting Man in the World” ad campaign. The other comics simply shake their heads in admiration.

For political junkies, there are plenty of Watergate jokes in earlier episodes, such as a 1974 introduction of Rickles as “the only civilian that was ever impeached,” or Rowan and Martin, in the Bicentennial year, mocking our nation’s only appointed Commander in Chief: “John Wayne has never run for president.” “Well, neither has Gerald Ford.” The shows often seem edited with Ginsu knives — occasionally, a roaster is welcomed to the dais but never makes it to the lectern. During the Davis roast, the diminutive song-and-dance man explodes twice in exactly the same gatemouth roar, 30 minutes apart, his hands flailing, a duplicate reaction shot meant to ensure that no viewer misses Sammy’s double-fisted bling collection.

In his Dino biography, Tosches is cruelly melancholy on the Celebrity Roast sunset of Martin’s career, noting that some segments were taped at the NBC studio in Burbank and others at the MGM Grand in Las Vegas, which meant that “guests often delivered their lines to empty chairs or pretended spontaneous laughter at words that had been uttered in another state.” Lamenting the “ten-writer assembly line” that cranked out “canned happiness,” which he felt imbued the show with “the quality of a relentlessly monotonous and vaguely disquieting dream,” Tosches renders his ultimate judgment: “It was a dais of despair. They sat at banquet tables at either side of the podium: the undead of dreamland and the fleeting stars of the television seasons.”

But as critics sometimes do, Tosches was substituting his own expectations and disappointments for those of the fans. Sure, to a bare-knuckled Virgil of the shadowlands like himself, a nightclub bruiser such as Gleason was old hat. But for millions of viewers who knew Gleason best as the hard-luck Brooklyn bus driver with a heart of gold, it was a revelation to see his calmly menacing bulk lounging at the lectern with gold pinkie ring, gold cigarette case, gold lighter, and gold cufflinks all glittering. When he says to Russell, “Just think, if you were white, you coulda been Sammy Davis Jr.,” we glimpse the standup heavyweight as captured in “Pafko at the Wall,” Don DeLillo’s rip-roaring opener to his novel Underworld: “Gleason got his start doing insult comedy in blood buckets all over Jersey and is still an eager table comic — does it for free, does it for fun, and leaves shattered lives behind.”

Bingeing on the discs’ 12 episodes as opposed to viewing them spread out as they were over their original air dates reveals some lazy bits. A favorite Rickles routine runs, “I know [fill in name of celebrity on the dais] is a great [singer, comedian, athlete, etc]. How do I know this? Because ([he/she] told me so backstage just before the show.” But for the most part, despite repetition, Mr. Warmth’s delivery, expressions, and gestures all kill, whereas Rich Little’s imitations of Jimmy Stewart’s fractured speech quickly grow stale. And, love or disdain them, 1970s roastees like Bob Hope, Johnny Carson, and Lucille Ball are shining stars for the ages; by 1984, Joan Collins seems pretty low-wattage.

And so we are left with a final question: Was Dino really as smashed as he always appeared to be onstage? Among the scores of drunk jokes directed at the master of ceremonies, one from Brooks pretty much sums it up: “The last time you and I were side by side, somebody [hiccup] stepped on my tongue.” But after Martin’s death, on Christmas Day, 1995, his old friend and colleague Joey Bishop swore that there had never been any drinking during working hours. “He had, in his J&B bottle, apple cider.” If so, Martin’s drunkard persona was worthy of the Oscar he was never nominated for.

Martin’s enduring charm resided in his insouciant indifference. If the ultimate joke asks, “What is the meaning of life?” Dino’s style embodied the punchline “Who cares?”

So give him the last word, from the close of his very own roast. “I’ll remember this night,” [squint at cue card, smile] “until I get to my car.”